re: How do you feel if you sell a stock and then it keeps going higher?

Bought 20 K of my companies stock shortly after I started a new position. Sold before a split where I felt it may drop after the split. Got out at $219/share

Stock is currently around $480 A year later.

In other words, I feel your pain

All I know is if I had never sold any stock throughout my life I'd be retired by now.... I'm 46

Yeah can’t have what if mentality in investing or you will go crazy

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I just keep calculating the money I missed out on by not waiting stock has gone from $32 to $119 in 5 years.

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What you should really feel about is not buying Bitcoin when it was $300...

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You'll never go broke taking profits

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True but conditional

For instance-
If your intent to sell for a profit means that you spend the profits, you can go broke.

If your intent to sell the winner for a profit and buy a loser, you can lose it all.

So imo, let winners run because you don’t know if the next stock purchase will also be a winner…. And you have to pay taxes on the gains you had from the last winner…

Have a long term strategy based on your financial goals, time horizon and risk appetite. Stick to it (versus trying to predict the future).

You company’s stock has a role in it. If mine, its role would rarely exceed 3% of total portfolio value and never 5% of total portfolio value. And if it pays high dividends even less % (not tax efficient). It would be designated for a future financial outlay, eg retirement big vacation fund for 1st 10yrs of retirement or towards dream home etc.

Annual portfolio allocation rebalancing to keep to long term strategy.

Then I would put Benjamin Graham’s Intelligent Investor book under your pillow. Chapter 8 in particular.

Lost out on $16k with nvidia. Sold before is skyrocketed right before they did their stock split. It’s not life changing money but it’s a lot.

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I have been stock heavy in my investments and the last year to year and a half I decided to start dumping my company stock because it was at an all time high and now it just keeps going higher I know nobody can tell the future this is the first major transaction I have ever made and it just pisses me off. Traded shares at around $92 and then dumped more when it got to $106. This am it was around $119. I just keep calculating the money I missed out on by not waiting stock has gone from $32 to $119 in 5 years.

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It's one of the more confounding biases I've seen. In your example, sounds like you had X number of shares and you sold, say 0.5X of them. Rationally, you should want the stock to keep going up, as your net position is still long...and yet, many humans find themselves hoping for it to go down.

nm.